1-(4-acetylphenyl)-2-(phenylsulfonyl)ethanone | 1260149-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-acetylphenyl)-2-(phenylsulfonyl)ethanone
• 英文别名: 1-(4-Acetylphenyl)-2-(benzenesulfonyl)ethanone；1-(4-acetylphenyl)-2-(benzenesulfonyl)ethanone
• CAS: 1260149-71-0
• 化学式: C₁₆H₁₄O₄S
• 分子量: 302.351
• InChiKey: YTPQQMYLGXBNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4'-(2-trimethylsilylethynyl)acetophenone 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.36h， 生成 1-(4-acetylphenyl)-2-(phenylsulfonyl)ethanone
  参考文献：
  名称：

  室温下水中芳基炔烃纳米胶束中的有氧氧化

  摘要：

  基于纳米胶束碳氢化合物核内氧气的更高溶解度，在室温下在水中实现了芳基炔烃至 β-酮砜的无金属和过氧化物有氧氧化。提供了许多示例来说明广泛的官能团耐受性。整个过程是环保的，由相关的低 E 因子记录。

  DOI：

  10.1002/anie.201310634

文献信息

• Manganese(III)-Mediated and -Catalyzed Decarboxylative Hydroxysulfonylation of Arylpropiolic Acids with Sodium Sulfinates in Water
  作者：Yan-Shi Xiong、Jiang Weng、Gui Lu

  DOI：10.1002/adsc.201701209

  日期：2018.4.17

  With water as both solvent and reactant, a novel manganese(III)‐mediated and ‐catalyzed synthesis of β‐ketosulfones through decarboxylative hydroxysulfonylation reactions of arylpropiolic acids with sodium sulfinates is described. This protocol has the advantages of mild reaction conditions, short reaction time, easy to handle reagents, purification simplicity, and being environmentally benign, which

  以水作为溶剂和反应物，描述了一种新的锰（III）介导和催化的芳基丙酸与亚磺酸钠的脱羧羟基磺酰化反应合成β-酮砜的方法。该方案的优点是反应条件温和，反应时间短，试剂易于操作，纯化简单且对环境无害，这证明了该方法的实用性。
• Rhodium(I)-Catalyzed Addition of Arylboronic Acids to (Benzyl-/Arylsulfonyl)acetonitriles: Efficient Synthesis of (<i>Z</i>)-β-Sulfonylvinylamines and β-Keto Sulfones
  作者：Gavin Chit Tsui、Quentin Glenadel、Chan Lau、Mark Lautens

  DOI：10.1021/ol102598p

  日期：2011.1.21

  An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.

  描述了一种有效的铑（I）催化的芳基硼酸加成到（苄基-/芳基磺酰基）乙腈中。以立体选择性的方式（Z-烯烃）形成新的β-磺酰基乙烯基胺产物。水解后，可获得有用的具有广泛范围的芳基和磺酰基取代基的β-酮砜。
• Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward β-Keto Sulfones
  作者：Qingquan Lu、Jian Zhang、Ganglu Zhao、Yue Qi、Huamin Wang、Aiwen Lei

  DOI：10.1021/ja4052685

  日期：2013.8.7

  An unprecedented dioxygen-triggered oxidative radical process was explored using dioxygen as the solely terminal oxidant, realizing aerobic oxidaitve difunctionalization of terminal alkynes toward beta-keto sulfones with high selectivity. Operando IR experiments revealed that pyridine not only acts as a base to successfully surpress ATRA (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.
• Aerobic Oxidation in Nanomicelles of Aryl Alkynes, in Water at Room Temperature
  作者：Sachin Handa、James C. Fennewald、Bruce H. Lipshutz

  DOI：10.1002/anie.201310634

  日期：2014.3.24

  On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β‐ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors.

  基于纳米胶束碳氢化合物核内氧气的更高溶解度，在室温下在水中实现了芳基炔烃至 β-酮砜的无金属和过氧化物有氧氧化。提供了许多示例来说明广泛的官能团耐受性。整个过程是环保的，由相关的低 E 因子记录。